In 1916, Rosa Rolanda began her artistic career in New York as a celebrated dancer in Broadway revues. She became involved with the Mexican artist Miguel Covarrubias in 1924, and in the following year the couple traveled to Mexico, where Rolanda began to take photographs.

During the late 1920s or early 1930s, Rolanda experimented with photograms, creating significant series of surrealist self-portraits that may have been influenced by Man Ray, who photographed Rolanda in Paris in 1923.

She probably began painting around 1926. The majority of Rolanda’s canvases depict colorful, folkloric scenes of children and festivals, portraits of friends such as the movie actresses Dolores del Río and María Félix, and self-portraits.

Rolanda and Covarrubias married in 1930, and by 1935 they had permanently settled into his family home in Tizapan El Alto, close to Mexico City.